165059-42-7

Basic information

• Product Name: (E)-2-(3-METHOXY-1-PROPEN-1-YL)-4 4 5 5&
• Synonyms: (E)-2-(3-METHOXY-1-PROPEN-1-YL)-4 4 5 5&;trans-3-Methoxy-1-propenylboronic acid pinacol ester, 95%;(e)-2-(3-methoxy-1-propen-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;(E)-3-Methoxy-1-propen-1-ylboronic acid, pinacol ester;trans-3-Methoxy-1-propenylboronic acid pinacol ester 95%;2-(3-Methoxyprop-1-en-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• CAS NO: 165059-42-7
• Molecular Formula: C₁₀H₁₉BO₃
• Molecular Weight: 198.07
• Mol File: 165059-42-7.mol

Chemical Properties

• Boiling Point: 229-230 °C(lit.)
• Flash Point: 214 °F
• Appearance: /
• Density: 0.933 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.279mmHg at 25°C
• Refractive Index: n20/D 1.4430(lit.)
• CAS DataBase Reference: (E)-2-(3-METHOXY-1-PROPEN-1-YL)-4 4 5 5&(CAS DataBase Reference)
• NIST Chemistry Reference: (E)-2-(3-METHOXY-1-PROPEN-1-YL)-4 4 5 5&(165059-42-7)
• EPA Substance Registry System: (E)-2-(3-METHOXY-1-PROPEN-1-YL)-4 4 5 5&(165059-42-7)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 165059-42-7(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(E)-2-(3-METHOXY-1-PROPEN-1-YL)-4 4 5 5& is used as a building block for the synthesis of various pharmaceuticals, contributing to the development of new drugs and therapeutic agents. Its unique chemical structure allows for versatile reactions and modifications, enabling the creation of diverse pharmaceutical compounds with potential medicinal properties.
Used in Agrochemical Industry:
In the agrochemical industry, (E)-2-(3-METHOXY-1-PROPEN-1-YL)-4 4 5 5& is utilized as a key intermediate in the synthesis of agrochemicals, such as pesticides and herbicides. Its reactivity and functional groups make it suitable for the development of effective and targeted agrochemicals that can improve crop protection and yield.
Used in Fine Chemicals Synthesis:
(E)-2-(3-METHOXY-1-PROPEN-1-YL)-4 4 5 5& is employed as a reagent in the preparation of various fine chemicals, including specialty chemicals, fragrances, and dyes. Its versatility in organic synthesis allows for the production of a wide range of high-value chemicals with specific applications in different industries.
Used in Organic Synthesis:
As a boronic ester derivative, (E)-2-(3-METHOXY-1-PROPEN-1-YL)-4 4 5 5& is used in organic synthesis to facilitate various chemical reactions, such as Suzuki-Miyaura cross-coupling reactions. This allows for the formation of new carbon-carbon bonds and the synthesis of complex organic molecules with potential applications in various fields.

InChI:InChI=1/C10H19BO3/c1-9(2)10(3,4)14-11(13-9)7-6-8-12-5/h6-7H,8H2,1-5H3/b7-6+

Upstream product

• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 
• 627-41-8 propargyl alcohol methyl ether 
• 73183-34-3 bis(pinacol)diborane 

Downstream Products

• 1026786-84-4 3-hydroxy-5-[(1E)-3-(methyloxy)-1-propen-1-yl]benzaldehyde 
• 1026787-07-4 methyl 3,5-bis((1E)-3-methoxy-prop-1-en-1-yl)-benzoate 
• 1140918-69-9 N-{(3E)-5-tert-butyl-1-methyl-2-[(2R)-tetrahydrofuran-2-ylmethyl]-1,2-dihydro-3H-pyrazol-3-ylidene}-2-[(1E)-3-methoxyprop-1-enyl]-5-(trifluoromethyl)benzamide 
• 1190979-40-8 (E)-5-ethyl-2-(4-(2-(3-methoxyprop-1-enyl)-4-((4-(methylsulfonyl)piperazin-1-yl)methyl)phenoxy)piperidin-1-yl)pyrimidine 
• 1255713-19-9 2-[4-((E)-3-methoxy-propenyl)-phenyl]-8-(2-trifluoromethoxybenzenesulfonyl)-2,8-diaza-spiro[4.5]decan-1-one 
• 1266477-07-9 (E)-N-(5-cyclopropyl-1H-pyrazol-3-yl)-5-(3-methoxyprop-1-enyl)-2-phenyl-pyrimidin-4-amine 
• 1255651-89-8 methyl (E)-2-(3-methoxyprop-1-en-1-yl)benzoate 
• 295349-46-1 methyl 4-(3-methoxypropyl)benzoate 
• 1409947-13-2 (E)-N-(2-(4-fluorophenyl)-2-methylpropyl)-3-(3-methoxyprop-1-en-1-yl)-1,2,4-thiadiazol-5-amine 
• 1223461-29-7 C₁₄H₁₈O₄ 
• 1223461-71-9 C₁₃H₁₅ClO₃ 

Relevant articles and documents

Solvent- and metal-free hydroboration of alkynes under microwave irradiation

Boronic esters are versatile building blocks extensively used in organic chemistry and essential to a variety of coupling reactions. In this work, the hydroboration reactions of alkynes were performed without metal catalysts using concomitant microwave ir

Chemoselective Cross-Coupling of gem-Borazirconocene Alkanes with Aryl Halides

The direct and chemoselective conversion of the carbon-metal bond of gem-dimetallic reagents enables rapid and sequential formation of multiple carbon-carbon and carbon-heteroatom bonds, thus representing a powerful method for efficiently increasing structural complexity. Herein, we report a visible-light-induced, nickel-catalyzed, chemoselective cross-coupling reaction between gem-borazirconocene alkanes and diverse aryl halides, affording a wide range of alkyl Bpin derivatives in high yields with excellent regioselectivity. This practical method features attractively simple reaction conditions and a broad substrate scope. Additionally, we systematically investigated a Bpin-directed chain walking process underlying the regioselectivity of alkylzirconocenes, thus uncovering the mechanism of the remote functionalization of internal olefins achieved with our method. Finally, DFT calculations indicate that the high regioselectivity of this reaction originates from the directing effect of the Bpin group.

One-Pot, Three-Step Synthesis of Cyclopropylboronic Acid Pinacol Esters from Synthetically Tractable Propargylic Silyl Ethers

Simple propargylic silyl ethers can be converted to complex cyclopropylboronic acid pinacol esters in an efficient one-pot procedure. Terminal acetylenes undergo a Schwartz's reagent catalyzed hydroboration; subsequent addition of further Schwartz's reage

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Silver-catalyzed highly regioselective formal hydroboration of alkynes

A silver(I)-N-heterocyclic carbene complex has proven to be a potent catalyst for formal hydroboration of alkynes, providing a variety of borylalkenes in regio- and stereoselective manners. Under the silver catalysis, allenes also undergo regioselective hydroboration to give borylalkenes.

Preparation of (E)-1-alkenylboronic acid pinacol esters via transfer of alkenyl group from boron to boron

Two synthetic routes to (E)-1-alkenylboronic acid pinacol esters 3 were investigated. Hydroboration of 1-alkynes 1 with 1,3,2-benzodioxaborole (catecholborane), in situ generated by the reaction of BH3 in THF with catechol, proceeded in the presence of a catalytic amount of dicyclohexylborane in THF at room temperature to give the corresponding (E)-1-alkenylboronic acid catechol esters 2. Treatment of the resultant esters 2 with 2,3-dimethyl-2,3-butanediol (pinacol) easily afforded the desired products 3, which are insensitive to air, moisture and chromatography, in good to high overall yields. The sequential reaction is a highly efficient route to 3 from BH3 in THF in a one-pot manner. Alternatively, hydroboration of 1 with 4,4,5,5-tetramethyl-1,3,2-dioxaborolane (pinacolborane) was achieved in the presence of a catalytic amount of dicyclohexylborane at room temperature under neat conditions to afford the corresponding products 3 directly in good to excellent yields. This route is extremely efficient and environmentally benign from the viewpoints of making good use of pinacolborane and of using no solvent, and is capable of using a variety of alkynes 1 including functionalized ones such as HCCCH2Cl and HCCCH2OTHP.

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